South Side Trips (flight + hotel)

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Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Chicago Museum of Science and Industry

Hyde Park

4 out of top 10 points of interest in this area

Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.

Find hotels in Hyde Park

Top hotels in South Side

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P4,750 per night from 9 Mar to 10 Mar
P4,750
P5,576 total
includes taxes & fees
Mar 9 - Mar 10
8.6/10 Excellent! (3,801 reviews)
"Biggest downsides to the property is that you are adjacent to Wacker and Michigan - both have high possibilities for noise (sirens, honking, etc) which I dealt with during my stay. Good dining options in the area, many within a 5 minute walk. Room size was fairly compact, but for a one night stay ..."

Reviewed on Feb 17, 2025

River Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P4,988 per night from 23 Feb to 24 Feb
P4,988
P5,855 total
includes taxes & fees
Feb 23 - Feb 24
7.8/10 Good! (8,509 reviews)
"A comfortable historical hotel, enjoyed the bar area, cocktails were good , would not recommend dining at the hotel. On Expedia it says it has parking and in and out privileges but this is not true, once you park you cant leave unless paying again (62$) . Had a paranormal experience in room 917 so ..."

Reviewed on Feb 18, 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P7,484 per night from 23 Feb to 24 Feb
P7,484
P8,786 total
includes taxes & fees
Feb 23 - Feb 24
9.6/10 Exceptional! (1,661 reviews)
"Nice place but can be noisy."

Reviewed on Feb 19, 2025

L7 Chicago by LOTTE
See all 4,847 properties in South Side
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a South Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in South Side from just . And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to South Side?
Book everything in the one place with our South Side vacation packages. You’ll find deals on flights, hotels and more that’ll keep your pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you’ll have the flexibility to mix and match all you want.
What are the top hotels in South Side?
When it comes to properties in Carville, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are a couple of favorites. If you’re considering heading to Chatham Fields, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my South Side vacation?
While not all airlines advertise ticket prices early, it’s usually possible to look up international flights on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you’re purchasing tickets last minute, there’s a chance you could get lucky. Sometimes the lowest prices become available a few weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has everything you need to book your South Side escape, but what your package looks like is up to you. Choose from a combination of rental cars, hotels and flights. Searching for some activities to keep you busy? Once you’ve made your booking, you can add them on too. Whatever your style or budget, there’s a package deal to suit your needs.
What should I know before booking a South Side travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we’re a one-stop shop for all of them. You’ll save precious cash just for combining your bookings. Whether you’re embarking on a ski trip or relaxing on a sunny beach, your perfect getaway is only clicks away.
Can I choose my airline with a South Side Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from all over the world. With so many choices, finding the right carrier to bring you to South Side will be a snap.
If I'm not able to travel, can I cancel my South Side vacation package?
You can. We get that even the best-laid plans can go awry, so we’re here to help if you have to make changes to your South Side vacation package. It may be possible to amend or cancel your itinerary for free if you’ve booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Popular places to visit

Chicago Museum of Science and Industry

Chicago Museum of Science and Industry

A large museum close to downtown Chicago with plenty for all ages to see and do, with exhibits including a coal mine and World War II submarine.

Chicago Museum of Science and Industry

What to do in South Side

Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

P1,692
per adult
86% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

P2,392
per adult
Field Museum of Natural History All-Access Pass
Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

P3,268
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
See all activities in South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.